EP1020457A1 - Verfahren zur Herstellung von polyfunktionellen Polycarbonat-oligomern,und ihren enthaltenden Polymeren - Google Patents
Verfahren zur Herstellung von polyfunktionellen Polycarbonat-oligomern,und ihren enthaltenden Polymeren Download PDFInfo
- Publication number
- EP1020457A1 EP1020457A1 EP99100586A EP99100586A EP1020457A1 EP 1020457 A1 EP1020457 A1 EP 1020457A1 EP 99100586 A EP99100586 A EP 99100586A EP 99100586 A EP99100586 A EP 99100586A EP 1020457 A1 EP1020457 A1 EP 1020457A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- oligomers
- epoxy
- cyclocarbonate
- polyfunctional
- reaction
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims description 22
- 229920000642 polymer Polymers 0.000 title description 5
- 230000015572 biosynthetic process Effects 0.000 title description 2
- 238000003786 synthesis reaction Methods 0.000 title description 2
- 238000006243 chemical reaction Methods 0.000 claims abstract description 22
- 150000004984 aromatic diamines Chemical class 0.000 claims abstract description 9
- 125000003700 epoxy group Chemical group 0.000 claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims description 6
- 239000004848 polyfunctional curative Substances 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims 2
- 125000002877 alkyl aryl group Chemical group 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 125000004103 aminoalkyl group Chemical group 0.000 claims 1
- 229920002601 oligoester Polymers 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- 239000003251 chemically resistant material Substances 0.000 abstract description 2
- 239000000203 mixture Substances 0.000 description 30
- 239000004593 Epoxy Substances 0.000 description 15
- 238000000576 coating method Methods 0.000 description 11
- 239000000853 adhesive Substances 0.000 description 9
- 230000001070 adhesive effect Effects 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- 239000003822 epoxy resin Substances 0.000 description 8
- 229920000647 polyepoxide Polymers 0.000 description 8
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 7
- 239000000565 sealant Substances 0.000 description 7
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 239000002131 composite material Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 229920002635 polyurethane Polymers 0.000 description 5
- 239000004814 polyurethane Substances 0.000 description 5
- 150000003139 primary aliphatic amines Chemical class 0.000 description 5
- 150000003141 primary amines Chemical class 0.000 description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- 229910000831 Steel Inorganic materials 0.000 description 4
- 239000010959 steel Substances 0.000 description 4
- HLBLWEWZXPIGSM-UHFFFAOYSA-N 4-Aminophenyl ether Chemical compound C1=CC(N)=CC=C1OC1=CC=C(N)C=C1 HLBLWEWZXPIGSM-UHFFFAOYSA-N 0.000 description 3
- -1 Inc(USA) Polymers 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229910002092 carbon dioxide Inorganic materials 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 229920003986 novolac Polymers 0.000 description 3
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 3
- 239000004810 polytetrafluoroethylene Substances 0.000 description 3
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 2
- KUBDPQJOLOUJRM-UHFFFAOYSA-N 2-(chloromethyl)oxirane;4-[2-(4-hydroxyphenyl)propan-2-yl]phenol Chemical compound ClCC1CO1.C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 KUBDPQJOLOUJRM-UHFFFAOYSA-N 0.000 description 2
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 2
- IHFQGEDFEXGPFR-UHFFFAOYSA-N 5-[4-(4-heptylbenzoyl)phenyl]pentanoic acid Chemical compound C1=CC(CCCCCCC)=CC=C1C(=O)C1=CC=C(CCCCC(O)=O)C=C1 IHFQGEDFEXGPFR-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 239000006260 foam Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- KMBPCQSCMCEPMU-UHFFFAOYSA-N n'-(3-aminopropyl)-n'-methylpropane-1,3-diamine Chemical compound NCCCN(C)CCCN KMBPCQSCMCEPMU-UHFFFAOYSA-N 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 229920000515 polycarbonate Polymers 0.000 description 2
- 239000004417 polycarbonate Substances 0.000 description 2
- 239000002990 reinforced plastic Substances 0.000 description 2
- 230000035939 shock Effects 0.000 description 2
- HGXVKAPCSIXGAK-UHFFFAOYSA-N 2,4-diethyl-6-methylbenzene-1,3-diamine;4,6-diethyl-2-methylbenzene-1,3-diamine Chemical compound CCC1=CC(CC)=C(N)C(C)=C1N.CCC1=CC(C)=C(N)C(CC)=C1N HGXVKAPCSIXGAK-UHFFFAOYSA-N 0.000 description 1
- DGRGLKZMKWPMOH-UHFFFAOYSA-N 4-methylbenzene-1,2-diamine Chemical compound CC1=CC=C(N)C(N)=C1 DGRGLKZMKWPMOH-UHFFFAOYSA-N 0.000 description 1
- 229920003319 Araldite® Polymers 0.000 description 1
- XWNOHVUYDRUFJW-UHFFFAOYSA-N CC[IH]1=CC(Br)=CC(C)=C1 Chemical compound CC[IH]1=CC(Br)=CC(C)=C1 XWNOHVUYDRUFJW-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229920000271 Kevlar® Polymers 0.000 description 1
- VCUFZILGIRCDQQ-KRWDZBQOSA-N N-[[(5S)-2-oxo-3-(2-oxo-3H-1,3-benzoxazol-6-yl)-1,3-oxazolidin-5-yl]methyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C1O[C@H](CN1C1=CC2=C(NC(O2)=O)C=C1)CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F VCUFZILGIRCDQQ-KRWDZBQOSA-N 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- FDLQZKYLHJJBHD-UHFFFAOYSA-N [3-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=CC(CN)=C1 FDLQZKYLHJJBHD-UHFFFAOYSA-N 0.000 description 1
- 150000004645 aluminates Chemical class 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 239000004568 cement Substances 0.000 description 1
- 239000011247 coating layer Substances 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N iron oxide Inorganic materials [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 239000004761 kevlar Substances 0.000 description 1
- 239000002649 leather substitute Substances 0.000 description 1
- 229940018564 m-phenylenediamine Drugs 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000004005 microsphere Substances 0.000 description 1
- QHJABUZHRJTCAR-UHFFFAOYSA-N n'-methylpropane-1,3-diamine Chemical compound CNCCCN QHJABUZHRJTCAR-UHFFFAOYSA-N 0.000 description 1
- BGTAKZMFBUNDSV-UHFFFAOYSA-N n,n'-bis(2-ethylphenyl)methanediamine Chemical compound CCC1=CC=CC=C1NCNC1=CC=CC=C1CC BGTAKZMFBUNDSV-UHFFFAOYSA-N 0.000 description 1
- WTSXICLFTPPDTL-UHFFFAOYSA-N pentane-1,3-diamine Chemical compound CCC(N)CCN WTSXICLFTPPDTL-UHFFFAOYSA-N 0.000 description 1
- 239000002986 polymer concrete Substances 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000011150 reinforced concrete Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000009864 tensile test Methods 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 229920006305 unsaturated polyester Polymers 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
- C08G65/2618—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing nitrogen
- C08G65/2621—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing nitrogen containing amine groups
- C08G65/2627—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing nitrogen containing amine groups containing aromatic or arylaliphatic amine groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/32—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D317/34—Oxygen atoms
- C07D317/36—Alkylene carbonates; Substituted alkylene carbonates
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/04—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers only
- C08G65/22—Cyclic ethers having at least one atom other than carbon and hydrogen outside the ring
Definitions
- the present invention is related to cyclocarbonate oligomers and polymer compounds based on them and, more specifically, to coatings, adhesives, composite materials, sealants, and synthetic leather and to methods of producing such materials.
- Nonisocyanate polyurethane oligomers and polymers are the product of the reaction of cyclocarbonate oligomers and primary amine oligomers. Typically the cyclocarbonate oligomer react with the primary aliphatic amine oligomer. By this reaction a cross-linked network polymer structure results in which an intermolecular hydrogen bond is formed through the hydroxyl group at the ⁇ -carbon atom of the polyurethane chain.
- Nonisocyanate polyurethane materials using aromatic amines and cyclocarbonates because of forming CO 2 and low molecular weight of compounds.
- One of the possible processes for making cyclocarbonates is a reaction between carbon dioxide and an epoxy compound in the presence of a catalyst.
- the chemically resistant materials with high mechanical properties are provided by using polycyclocarbonates of special structure.
- the polycyclocarbonates are prepared by the reaction of oligocyclocarbonates containing ended epoxy groups with primary aromatic diamine.
- One embodiment of the present invention relates to oligomers containing epoxy and cyclocarbonate groups, adduct of aromatic diamines with these oligomers.
- Such oligomers may be used by two ways - by curing the oligomers with primary aliphatic amines and by preparing adducts which are used for curing epoxy resins or cyclocarbonate oligomers for preparing constructive glues, sealants, coatings, construction, etc.
- Polycyclocarbonate oligomers of the present invention are based upon oligomers with epoxy and cyclocarbonate groups which ware prepared by the reaction of carbon dioxide and an epoxy oligomer with catalyst according our pat. (Patent Israel 122763)
- Such oligomers containing epoxy and cyclocarbonate groups react with aromatic diamines only by epoxy groups. It is possible to cure such cyclocarbonate oligomers by primary aliphatic amines and to prepare adducts of synthesised cyclocarbonates with primary aliphatic amines that are used as hardeners for epoxy oligomers.
- epoxy-cyclocarbonate olygomers preferably of such formula:
- aromatic diamines Preferably commercially available aromatic diamines: m-phenylendiamine, 4,4'-diaminodiphenylmethane, 4,4'-diaminodiphenyloxide, 2,4 and 2,6 diethyltoluelenediamine (Albermarle Corporation).
- Preferably commercially available primary amines N,N-bis(3-aminopropyl) methylamine (BASF, Germany), m-xylylenediamine (Mitsubishi, Japan), triethyleneglycoldiamine (Jeffamine), EDR-148 (Huntsman Corporation, USA), 1,3-diaminopentane (Du Pont, USA), Isoforondiamine (BASF, Germany), Jeffamine T-403 (Huntsman Corporation, USA), etc.
- Synthesis is a reaction between epoxy group of the oligomer and aromatic diamines. Such process is working out in special glass reactor under N 2 . Contents are mixed during 10 min at the 20°C, after that the reaction continues during 0,5-1 hr by the 120-130 °C. After this operation according with Table 1 primary amines are mixed with compounds after that the reaction continues during 2 hrs by the 110-120°C (samples 1,3,5,7,9). After that the oligomers are mixed with epoxy resins for curing (according Table 1).
- Oligomers (samples 2,4,6,8,10) are mixed with primary amines according Table 1 for curing.
- Cyclocarbonate oligomers (1-10) prepared according the method described in Example 1 were used to coat a cleaned steel plate. Each composition formed a coating layer with a thickness of 0,1-0,2 mm. Then the coating was hardened at a temperature 110°C for 2 hours. These coated steel samples were used to determine the adhesion of each coating to the steel substrate according to the method prescribed by ASTM D3359-93. Compositions were used as 80% solution in dimethylformamide. For the purposes of tensile testing, the above procedure was modified by using a polytetrafluoroethylene (PTFE) sheet instead of steel plate, so a free film of each of the 10 cyclocarbonate-oligomers could be obtained by peeling the PTFE from the cured film.
- PTFE polytetrafluoroethylene
- the tensile properties, i.e. tensile strength and elongation at break, of each free cured film were determined according to the method prescribed by ASTM D638-84. Such samples were also used to determine the coefficient of chemical resistance of each coating by the procedure discussed above in which the tensile strength was used to determine K CR .
- the proposed oligomers may be used for preparing adhesives, sealants, synthetic foams, synthetic leathers, hardeners for epoxy resins, casting elastomers, structure plastics, etc.
- Adhesives based on the compositions 1-10 can be used as structure adhesives with high service properties.
- the adhesives compositions have been received by adding to adducts (1, 3, 7 or 9) epoxy resins, which are using here as a hardener. By using the compositions 2, 3, 4 and 6-10 addition adding epoxy resins does not needed.
- Such method of Adhesives preparing gives adhesives joints with more shock and vibration resistance properties. The mechanical properties of adhesives joints were described in the table 2.
- pigments and fillers can be also added.
- Preferable ones are barium sulfate, titanium dioxide, silica and ferrous oxides pigments and aluminate cement.
- By adding as a filler glass microspheres can be received synthetic foams.
- Sealants can be received on the base of adducts by example 1, 3, 7. In this case are needed using another hardeners (see table 4). The properties of such sealants are given in the table 5.
- On the base on oligomers according to example 1-10 can be also prepared reinforced plastics with glass, carbon or kevlar fibers and polymerconcretes with high impact, shock and abrasive resistance, with 2-3 times higher mechanical properties than those of well known unsaturated polyester reinforced plastics and concretes.
- Compositions for Sealants (parts by weight).
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP99100586A EP1020457A1 (de) | 1999-01-14 | 1999-01-14 | Verfahren zur Herstellung von polyfunktionellen Polycarbonat-oligomern,und ihren enthaltenden Polymeren |
| AU11728/00A AU1172800A (en) | 1999-01-14 | 1999-11-24 | Cyclocarbonate groups containing hydroxyamine oligomers from epoxycyclocarbonates |
| US09/622,960 US6407198B1 (en) | 1999-01-14 | 1999-11-24 | Cyclocarbonate groups containing hydroxyamine oligomers from epoxycylclocarbonates |
| PCT/IB1999/001885 WO2000042033A1 (en) | 1999-01-14 | 1999-11-24 | Cyclocarbonate groups containing hydroxyamine oligomers from epoxycyclocarbonates |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP99100586A EP1020457A1 (de) | 1999-01-14 | 1999-01-14 | Verfahren zur Herstellung von polyfunktionellen Polycarbonat-oligomern,und ihren enthaltenden Polymeren |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| EP1020457A1 true EP1020457A1 (de) | 2000-07-19 |
Family
ID=8237345
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP99100586A Withdrawn EP1020457A1 (de) | 1999-01-14 | 1999-01-14 | Verfahren zur Herstellung von polyfunktionellen Polycarbonat-oligomern,und ihren enthaltenden Polymeren |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US6407198B1 (de) |
| EP (1) | EP1020457A1 (de) |
| AU (1) | AU1172800A (de) |
| WO (1) | WO2000042033A1 (de) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006010408A1 (de) * | 2004-07-22 | 2006-02-02 | Henkel Kommanditgesellschaft Auf Aktien | Zwei-komponenten-bindemittel |
| US8143346B2 (en) | 2003-08-13 | 2012-03-27 | Huntsman Advanced Materials Americas Llc | Nanocomposites based on polyurethane or polyurethane-epoxy hybrid resins prepared avoiding isocyanates |
| WO2014068251A1 (fr) * | 2012-11-05 | 2014-05-08 | Bostik Sa | Polymères de [4-(méthyléther)-1,3-dioxolane-2-one de polyéther polyol] |
| WO2015164692A1 (en) * | 2014-04-25 | 2015-10-29 | Valspar Sourcing, Inc. | Polycyclocarbonate compounds and polymers formed therefrom |
| US10179871B2 (en) | 2014-04-04 | 2019-01-15 | Henkel Ag & Co. Kgaa | Two-component binder system with cyclocarbonate and epoxy groups |
| US10717897B2 (en) | 2014-04-25 | 2020-07-21 | The Sherwin-Williams Company | Polycyclocarbonate compounds and polymers and compositions formed therefrom |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7232877B2 (en) * | 2001-10-01 | 2007-06-19 | Homecom Communications, Inc. | Preparation of oligomeric cyclocarbonates and their use in ionisocyanate or hybrid nonisocyanate polyurethanes |
| JP5069737B2 (ja) * | 2009-11-19 | 2012-11-07 | 大日精化工業株式会社 | 擬革 |
| US8604091B2 (en) | 2010-09-03 | 2013-12-10 | Owens Corning Intellectual Capital, Llc | Non-isocyanate spray foam |
| US9487662B1 (en) * | 2014-01-21 | 2016-11-08 | Nanotech Industries, Inc. | Radiation-curable biobased flooring compositions with nonreactive additives |
| WO2019164900A1 (en) | 2018-02-21 | 2019-08-29 | Cryovac, Llc | Method and formulation for an isocyanate-free foam using isocyanate-free polyurethane chemistry |
| US11822117B2 (en) * | 2019-10-08 | 2023-11-21 | Corning Incorporated | Primary coating compositions with improved microbending performance |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0303158A2 (de) * | 1987-08-08 | 1989-02-15 | Hoechst Aktiengesellschaft | Härtbare Verbindungen, deren Herstellung und Verwendung |
| US5175231A (en) * | 1992-04-17 | 1992-12-29 | Fiber-Cote Corporation | Urethane oligomers and polyurethanes |
| US5340889A (en) * | 1993-07-19 | 1994-08-23 | Texaco Chemical Company | Liquification of bis-carbonates of bis-glycidyl ethers |
| WO1998058004A1 (en) * | 1997-06-16 | 1998-12-23 | Mmr Technologies | Water-compatible urethane-containing amine hardener |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SU908769A1 (ru) * | 1978-01-06 | 1982-02-28 | Центральный научно-исследовательский и проектно-экспериментальный институт промышленных зданий и сооружений | Полимербетонна смесь |
| US4585566A (en) * | 1984-11-21 | 1986-04-29 | Chevron Research Company | Carbonate treated dispersants |
| DE3624314A1 (de) | 1986-07-18 | 1988-01-28 | Hoechst Ag | Verwendung von epoxidharz/haerter-mischungen zur herstellung von beschichtungen mit erhoehter zwischenschichthaftung |
| US5235007A (en) | 1991-10-03 | 1993-08-10 | Texaco Chemical Company | Epoxy curing agents |
-
1999
- 1999-01-14 EP EP99100586A patent/EP1020457A1/de not_active Withdrawn
- 1999-11-24 WO PCT/IB1999/001885 patent/WO2000042033A1/en active Search and Examination
- 1999-11-24 AU AU11728/00A patent/AU1172800A/en not_active Abandoned
- 1999-11-24 US US09/622,960 patent/US6407198B1/en not_active Expired - Fee Related
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0303158A2 (de) * | 1987-08-08 | 1989-02-15 | Hoechst Aktiengesellschaft | Härtbare Verbindungen, deren Herstellung und Verwendung |
| US5175231A (en) * | 1992-04-17 | 1992-12-29 | Fiber-Cote Corporation | Urethane oligomers and polyurethanes |
| US5340889A (en) * | 1993-07-19 | 1994-08-23 | Texaco Chemical Company | Liquification of bis-carbonates of bis-glycidyl ethers |
| WO1998058004A1 (en) * | 1997-06-16 | 1998-12-23 | Mmr Technologies | Water-compatible urethane-containing amine hardener |
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| US8143346B2 (en) | 2003-08-13 | 2012-03-27 | Huntsman Advanced Materials Americas Llc | Nanocomposites based on polyurethane or polyurethane-epoxy hybrid resins prepared avoiding isocyanates |
| WO2006010408A1 (de) * | 2004-07-22 | 2006-02-02 | Henkel Kommanditgesellschaft Auf Aktien | Zwei-komponenten-bindemittel |
| EP1771495A1 (de) | 2004-07-22 | 2007-04-11 | Henkel Kommanditgesellschaft Auf Aktien | Zwei-komponenten-bindemittel |
| US8118968B2 (en) | 2004-07-22 | 2012-02-21 | Henkel Ag & Co. Kgaa | Two-component bonding agent |
| WO2014068251A1 (fr) * | 2012-11-05 | 2014-05-08 | Bostik Sa | Polymères de [4-(méthyléther)-1,3-dioxolane-2-one de polyéther polyol] |
| FR2997700A1 (fr) * | 2012-11-05 | 2014-05-09 | Bostik Sa | Polymeres de [4-(methylether)-1,3-dioxolane-2-one de polyether polyol] |
| US10179871B2 (en) | 2014-04-04 | 2019-01-15 | Henkel Ag & Co. Kgaa | Two-component binder system with cyclocarbonate and epoxy groups |
| CN106459658A (zh) * | 2014-04-25 | 2017-02-22 | 威士伯采购公司 | 多环碳酸酯化合物以及由其形成的聚合物 |
| US10000461B2 (en) | 2014-04-25 | 2018-06-19 | Swimc Llc | Polycyclocarbonate compounds and polymers formed therefrom |
| WO2015164692A1 (en) * | 2014-04-25 | 2015-10-29 | Valspar Sourcing, Inc. | Polycyclocarbonate compounds and polymers formed therefrom |
| CN106459658B (zh) * | 2014-04-25 | 2019-04-23 | 宣伟投资管理有限公司 | 多环碳酸酯化合物以及由其形成的聚合物 |
| US10717897B2 (en) | 2014-04-25 | 2020-07-21 | The Sherwin-Williams Company | Polycyclocarbonate compounds and polymers and compositions formed therefrom |
| US10759773B2 (en) | 2014-04-25 | 2020-09-01 | Swimc Llc | Polycyclocarbonate compounds and polymers formed therefrom |
Also Published As
| Publication number | Publication date |
|---|---|
| US6407198B1 (en) | 2002-06-18 |
| AU1172800A (en) | 2000-08-01 |
| WO2000042033A1 (en) | 2000-07-20 |
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